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Sodium Bicarbonate → 4-Ethylphenyl-3-hydroxypyridin-2-yl-methanol

HRID 2116498
Notes
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Reaction equation

HRID 2116498 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[C:16]([O:17]COCC[Si](CC)(CC)CC)=[CH:15][CH:14]=[CH:13][N:12]=2)[OH:10])=[CH:5][CH:4]=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[OH:10])=[CH:7][CH:8]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 69220512HCID 69220512, compound

Product 1

HCID 231036174-Ethylphenyl-3-hydroxypyridin-2-yl-methanolYield 41.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-ethylphenyl-[3-[2-(triethylsilyl)ethoxymethoxy]]pyridin-2-yl-methanol (2.35 g, 6.54 mmol) in THF-water (25:1; 60 mL), p-toluenesulfonic acid monohydrate (2.8 g, 16.4 mmol) was added and stirred at room temperature for 20 hours and at 40° C. for 4 hours. After cooling the reaction mixture to room temperature, saturated sodium bicarbonate solution (100 mL) was added and the resulting mixture was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 4-ethylphenyl-3-hydroxypyridin-2-yl-methanol (0.62 g).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. extractionthe resulting mixture was then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-092eb62a49484917bc40e88e61630e6d
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07439232B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes